Hydrochloric Acid → HCID 69415319, compound

HRID 916946Notes

Reaction equation

HRID 916946 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17]C)=[O:16])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[CH:11][C:10]=1[C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10309568HCID 10309568, compound

Product 1

HCID 69415319HCID 69415319, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylate (170 mg, 0.43 mmol) from Example 61, Step B in methanol (5 mL) was added 5N sodium hydroxide (0.20 mL, 1.0 mmol). The reaction was stirred at rt for 20 h and was then acidified with 2N hydrochloric acid and extracted twice with methylene chloride. The organic layer was washed with a portion of brine, dried over sodium sulfate, and concentrated in vacuo to give 6-(2,4-dichlorophenyl)-5-(4-chlorophenyl)pyridine-3-carboxylic acid as a white solid. HPLC/MS: 378 (M+1), 380 (M+3); Rt=3.65 min

Workup

  1. extractionextracted twice with methylene chloride
  2. washThe organic layer was washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a20886b5b7249d4a93eaa2ba2527b36
Source dataset
uspto-grants-2007_09
Patent number
US07271266B2

Reaction notes

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